Fuel additive and fuel composition containing the same

ABSTRACT

A fuel additive containing an alkylene-oxide-adducted hydrocarbyl amide is disclosed. The alkylene-oxide-adducted hydrocarbyl amide is surprisingly useful for improving the acceleration response and the driving performance of internal combustion engines when used as fuel additives in hydrocarbon-based fuels, such as gasoline fuel or diesel fuel.

[0001] The present invention relates to a fuel additive containing analkylene-oxide-adducted hydrocarbyl amide. In a further aspect thepresent invention relates to the use of the fuel additive in ahydrocarbon-based fuel, such as gasoline fuel or diesel fuel, to enhancethe acceleration response and the driving performance of internalcombustion engines, such as gasoline or diesel engines.

BACKGROUND OF THE INVENTION

[0002] In order to increase engine output power and accelerationresponse of spark ignition engines in automobiles, various types ofoxygen-containing additives for hydrocarbon-based fuel have beeninvestigated. These hydrocarbon-based fuels include alcohol (e.g.methanol and ethanol), ether (e.g. methyl-t-butyl ether), and ketone(e.g. acetone). In addition, the use of additives, such as hydrazine ornitro compounds (for example nitromethane including nitropropane andnitroparaffin, or nitrobenzene) have been examined for automobileracing. However, the problem with using such additives is that theyoften have an adverse effect on the durability of the engine and itscomponents.

[0003] It is also known that organometallic compounds (e.g. tetraethyllead or similar lead alkyls:ferrocene, methyl cyclopentadienyl manganesetricarbonyl), as well as aromatic amine compounds (e.g. aniline,monomethyl aniline, or dimethyl aniline) can be used as anti-knockingagents. However, it has been confirmed that these compounds dramaticallyreduce the operating efficiency of three-way catalysts due to catalystpoisoning. Japanese Patent Application Number (Kokai) 58-104996(corresponding to U.S. Pat. No. 4,409,000) describes the use of an alkylamine or ethylene-oxide-adducted alkenyl amine as an additive inautomobile fuel to clean carburetors and engines.

[0004] According to European Patent Number 0869163 A1 it is possible toreduce friction in gasoline engines by adding N,N-bis(hydroxyalkyl)alkyl amine to gasoline.

[0005] According to PCT Patent Publication 2001-502374 (WO-98/17746),solubility in water as well as the engine performance can be improved byadding fatty acid diethanol amide, fatty acid ethoxylate and alcoholethoxylate to a liquid fuel such as gasoline or diesel fuel.

SUMMARY OF THE INVENTION

[0006] The present invention relates to a fuel additive containing analkylene-oxide-adducted hydrocarbyl amide. In a further aspect thepresent invention relates to the use of the fuel additive in ahydrocarbon-based fuel, such as gasoline fuel or diesel fuel, to enhancethe acceleration response and the driving performance of internalcombustion engines, such as gasoline or diesel engines.

[0007] In its broadest aspect, the present invention relates to a fueladditive comprising an alkylene-oxide-adducted hydrocarbyl amide havingfrom 3 to 50 moles of alkylene oxide per mole of hydrocarbyl amide.

[0008] In another aspect, the present invention relates to a fuelcomposition comprising a major amount of a hydrocarbon boiling in thegasoline or diesel range and, from 10 to 10,000 ppm weight per weight offuel, of the fuel additive of the present invention.

[0009] In still another aspect, the present invention relates to amethod of operating an automobile engine with the fuel composition ofthe present invention.

[0010] In a further aspect, the present invention relates to a method ofimproving the acceleration performance of a gasoline automobile enginecomprising additizing the fuel additive of the present invention to agasoline and operating the engine with the additized gasoline.

[0011] Among other factors, the present invention is based on thediscovery that certain alkylene-oxide-adducted hydrocarbyl amides aresurprisingly useful for improving the acceleration response and thedriving performance of internal combustion engines when used as fueladditives in hydrocarbon-based fuels, such as gasoline fuel or dieselfuel.

DETAILED DESCRIPTION OF THE INVENTION

[0012] As stated above, the present invention relates to a fuel additivecontaining an alkylene-oxide-adducted hydrocarbyl amide and its use as afuel additive in a hydrocarbon-based fuel, such as gasoline fuel ordiesel fuel.

[0013] Prior to discussing the present invention in detail, thefollowing terms will have the following meanings unless expressly statedto the contrary.

Definitions

[0014] The term “hydrocarbyl” refers to an organic radical primarilycomposed of carbon and hydrogen which may be aliphatic, alicyclic,aromatic or combinations thereof, e.g., aralkyl or alkaryl. Suchhydrocarbyl groups may also contain aliphatic unsaturation, i.e.,olefinic or acetylenic unsaturation, and may contain minor amounts ofheteroatoms, such as oxygen or nitrogen, or halogens, such as chlorine.When used in conjunction with carboxylic fatty acids, hydrocarbyl willalso include olefinic unsaturation.

[0015] The term “alkyl” refers to both straight- and branched-chainalkyl groups.

[0016] The term “lower alkyl” refers to alkyl groups having 1 to about 6carbon atoms and includes primary, secondary and tertiary alkyl groups.Typical lower alkyl groups include, for example, methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-pentyl, n-hexyl andthe like.

[0017] The term “alkenyl” refers to an alkyl group with unsaturation.

[0018] The term “alkylene oxide” refers to a compound having theformula:

[0019] wherein R₁ and R₂ are each independently hydrogen or lower alkylhaving from 1 to 6 carbon atoms.

[0020] The term “fuel” or “hydrocarbon-based fuel” refers to normallyliquid hydrocarbons having boiling points in the range of gasoline anddiesel fuels.

[0021] In its broadest aspect, the present invention involves a fueladditive comprising an alkylene-oxide-adducted hydrocarbyl amide havingfrom 3 to 50 moles, preferably from 3 to 20 moles, more preferably from4 to 15 moles, of alkylene oxide per mole of hydrocarbyl amide.

[0022] The alkylene-oxide-adducted hydrocarbyl amide of the presentinvention is derived from an alkyl amide having from 4 to 75, preferablyfrom 8 to 22, carbon atoms or alkenyl amide with at least one or twopoints of unsaturation having from 4 to 75, preferably from 8 to 22,carbon atoms. Examples of desirable alkyl amides suitable for thepresent invention include, but are not limited to, octyl amide (caprylamide), nonyl amide, decyl amide (caprin amide), undecyl amide dodecylamide (lauryl amide), tridecyl amide, teradecyl amide (myristyl amide),pentadecyl amide, hexadecyl amide (palmityl amide), heptadecyl amide,octadecyl amide (stearyl amide), nonadecyl amide, eicosyl amide (alkylamide), or docosyl amide (behenyl amide). Examples of desirable alkenylamides include, but are not limited to, palmitoolein amide, oleyl amide,isooleyl amide, elaidyl amide, linolyl amide, linoleyl amide.Preferably, the alkyl or alkenyl amide is a coconut oil fatty acidamide.

[0023] The alkylene oxide adducted to the hydrocarbyl amide of thepresent invention is derived from an alkylene group having from 2 to 5carbon atoms. Preferably, the alkylene oxide is selected from the groupconsisting of ethylene oxide, propylene oxide, butylene oxide, andpentylene oxide. Ethylene oxide and propylene oxide are particularlypreferred. In addition, mixtures of alkylene oxides are desirable inwhich, for example, a mixture of ethylene oxide and propylene oxide maybe used to form the alkylene-oxide-adducted hydrocarbyl amide of thepresent invention. A respective molar ratio of from 1:5 to 5:1 may beused in the case of a mixture of ethylene oxide and propylene oxide.

[0024] A desirable number of moles of the alkylene oxide to be adductedto the hydrocarbyl amide will be in the range of from 3 to 50 moles ofalkylene oxide per 1 mole of hydrocarbyl amide. More preferably, therange of from 3 to 20 moles is particularly desirable. Most preferably,the range of from 4 to 15 moles is most preferable as a molar range ofthe additive.

[0025] Preferably, the alkylene-oxide adducted hydrocarbon amide isderived from an alkylene-oxide-adduction reaction involving a coconutoil fatty acid amide with ethylene oxide and propylene oxide. However,the alkylene-oxide adducted hydrocarbyl amides useful as fuel additivesin the present invention can be also a mixed product wherein varioustypes and different moles of alkylene oxide and can be adducted tovarious types of hydrocarbyl amides.

[0026] The present invention provides for a method of operating gasolineengine automobiles wherein an automobile equipped with a gasoline engineis operated with the fuel composition of the present invention. Themethod of operating gasoline engine automobiles is preferred when theamount of alkylene oxide is from 3 to 20 moles per mole of hydrocarbylamide and the alkylene oxide is selected from the group consisting ofethylene oxide, propylene oxide, butylene oxide, pentylene oxide, ormixtures thereof.

[0027] The present invention further provides for a method of improvingthe driving and acceleration performance of internal combustion engines,such as a gasoline or diesel engines in automobiles, by using the fueladditive described herein.

[0028] The fuel additive of the present invention improves accelerationperformance of internal combustion engines when the fuel additive isadded to a low boiling point hydrocarbon-based fuel like gasoline, andthe driving performance is also improved when the additive is added toother hydrocarbon-based fuel like a diesel fuel, alcohol fuel or etherfuel. The method of improving acceleration performance in gasolineengine automobiles is preferred when the amount of alkylene oxide isfrom 3 to 20 moles per mole of hydrocarbyl amide and the alkylene oxideis selected from the group consisting of ethylene oxide, propyleneoxide, butylene oxide, pentylene oxide, or mixtures thereof.

[0029] The amount of fuel additive of the present invention added in ahydrocarbon-based fuel will typically be in a range of from 10 to 10,000ppm weight per weight (active component ratio). More preferably, thedesired range is from 10 to 5,000 ppm weight per weight, while a rangeof from 10 to 1,000 ppm weight per weight is most preferable.

[0030] The fuel additive of the present invention is normally suppliedas an organic solvent solution with an effective fuel additive contentof at least 30 weight %, based on the amount of the fuel additive andorganic solvent solution.

[0031] Although no particular limitations are imposed on the method usedto add a fuel additive of the present invention to a hydrocarbon-basedfuel, a concentrated fuel additive product may be prepared whichcontained at least 30 weight % of the active component. This product canbe added according to any selected method including adding it into thefuel tank of a fuel station or into the fuel tank of a passenger car.

[0032] The fuel additive of the present invention can also be combinedwith one, two, or more other additives publicly known to be used inhydrocarbon-based fuels. Such additives include, but are not limited to,deposit control additives such as detergents or dispersants, corrosioninhibitors, oxidation inhibitors, metal deactivators, corrosioninhibitors, demulsifiers, static electricity preventing agents,anti-coagulation agents, anti-knock agents, oxygenates, flow improvers,pour point depressants, cetane improvers and auxiliary-solution agents.

EXAMPLES

[0033] The invention will be further illustrated by the followingexamples, which set forth particularly advantageous method embodiments.While the examples are provided to illustrate the present invention,they are not intended to limit it. The present invention has beendescribed with reference to specific embodiments and it is intended tocover those various changes and substitutions that may be made by thoseskilled in the art without departing from the spirit and scope of theappended claims.

Example 1

[0034] A Toyota Camry 1800 cc, 5MT (Type E-SV40, provided with KnockSensor, type 4S-FE engine), mounted on a chassis dynamometer, wasoperated at a constant speed of 20 km/hr. The acceleration measurementwas initiated by fully opening the throttle and measuring the amount oftime required for the vehicle speed to reach 110 km/hr with thetransmission locked in fourth gear. This measurement was repeated 10times using the same fuel and the median value obtained from these 10measurements was determined as the acceleration time period. Inaddition, in order to minimize the influence of ambient conditions(temperature, pressure, etc.) on engine performance, the entire testprocedure was executed within a single day.

[0035] The gasoline used have the following specifications: density (at15° C.): 0.7389 g/cm³, Reid vapor pressure: 60.5 Kpa, octane number:90.2 (RON), 82.3 (MON), aromatics (volume %): 29.9, olefin (volume %):15.6, 10% distillation temperature (° C.): 50.0, 50% distillationtemperature (° C.): 92.0, 90% distillation temperature (° C.): 169.5.The fuel composition was adjusted by adding 100 mg/L of 5 moles of oleylamide-ethylene oxide (fuel additive) to this gasoline.

[0036] Gasoline containing the above described fuel additive andgasoline without the fuel additive (same as the above) were then testedin accordance with the test procedures described herein above. Table 1shows the results. TABLE 1 Test Fuel Oil Acceleration Time Period(20-110 km/hours) Gasoline with No Additive 24.91 seconds (ComparativeExample) Fuel Composition 24.69 seconds containing Additive

[0037] From the different acceleration time periods shown in Table 1, itis clear that the acceleration performance was improved by the fueladditive of the present invention. Although the difference in theacceleration time period indicated in Table 1 is not dramatic (less than1%) with the fuel additive of the present invention, this is a distinctdifference, particularly in case of cars needing to attain a high speed,such as racing cars, etc. Furthermore, in addition to the importance ofacceleration for racing cars, even a small improvement in accelerationperformance can be very important for passenger cars driving on publicroads where it may be necessary to suddenly accelerate in order to avoidan accident, etc., as a result of a sudden event.

Example 2

[0038] The test was carried out as described in Example 1, using fourmoles of propylene oxide adducted coconut oil fatty acid di-ethanolamide (fuel additive) was added at a concentration of 100 mg/L to thisgasoline in order to prepare a fuel composition containing the fueladditive.

[0039] Gasoline containing the above described fuel additive andgasoline without the fuel additive (same as the above) were then testedin the acceleration evaluation test in accordance with the testprocedures described in Example 1. Table 2 shows the results of thetest. TABLE 2 Test Fuel Oil Acceleration Time Period (20-110 km/hours)Gasoline with No Additive 24.51 seconds (Comparative Example) FuelComposition 24.38 seconds containing Additive

[0040] As shown by the results in Table 2, the acceleration performancewas clearly improved when the fuel additive of the present invention wasemployed in the fuel.

Example 3

[0041] The test was carried out as described in Example 1, using tenmoles of propylene oxide adducted coconut oil fatty acid di-ethanolamide (fuel additive) was added to provide a concentration of 100 mg/Lin this gasoline in order to prepare a fuel composition containing thefuel additive.

[0042] Gasoline containing the above described fuel additive andgasoline without fuel additive (same as the above) were then tested inaccordance with the test procedures described previously. Table 3 showsthe results of the test. TABLE 3 Test Fuel Oil Acceleration Time Period(20-110 km/hours) Gasoline with No Additive 24.85 seconds (ComparativeExample) Fuel Composition 24.74 seconds containing Additive

[0043] As shown by the results in Table 3, the acceleration performancewas clearly improved when the fuel additive of the present invention wasemployed in the fuel.

Example 4

[0044] The test was carried out as described in Example 1 except thegasoline used had the following specifications: density 9 at 15° C.:0.7303 g/cm³, Reid vapor pressure: 60.2Kpa, octane number: 92.1 (RON),aromatics (volume %): 23.19, olefin (volume %) 19, 10% distillationtemperature (° C.): 54.3, 50% distillation temperature (° C.): 86.2, 90%distillation temperature (° C.): 158.1 and using four moles of propyleneoxide and two moles of ethylene oxide adducted coconut oil fatty aciddi-ethanol amide (fuel additive) were added to provide a concentrationof 100 mg/L in this gasoline.

[0045] Gasoline containing the above described fuel additive andgasoline without fuel additive (same as the above) were then tested inaccordance with the test procedures described previously. Table 4 showsthe results of the test. TABLE 4 Test Fuel Oil Acceleration Time Period(20-110 km/hours) Gasoline with No Additive 23.96 seconds (ComparativeExample) Fuel Composition 23.75 seconds containing Additive

[0046] As shown by the results in Table 4, the acceleration performancewas clearly improved when the fuel additive of the present invention wasemployed in the fuel.

What is claimed is:
 1. A fuel additive comprising analkylene-oxide-adducted hydrocarbyl amide having from 3 to 50 moles ofalkylene oxide per mole of hydrocarbyl amide.
 2. The fuel additiveaccording to claim 1, wherein the alkylene-oxide-adducted hydrocarbylamide has from 3 to 20 moles of alkylene oxide per mole of hydrocarbylamide.
 3. The fuel additive according to claim 2, wherein thealkylene-oxide-adducted hydrocarbyl amide has from 4 to 15 moles ofalkylene oxide per mole of hydrocarbyl amide.
 4. A fuel additiveaccording to claim 1, wherein the alkylene-oxide-adducted hydrocarbylamide is derived from an alkyl or alkenyl amide having from 4 to 75carbon atoms.
 5. A fuel additive according to claim 4, wherein thealkylene-oxide-adducted hydrocarbyl amide is derived from an alkyl oralkenyl amide having from 8 to 22 carbon atoms.
 6. A fuel additiveaccording to claim 5, wherein the alkyl or alkenyl amide is a coconutoil fatty acid amide.
 7. A fuel additive according to claim 1, whereinthe alkylene oxide is selected from the group consisting of ethyleneoxide, propylene oxide, butylene oxide, pentylene oxide, or mixturesthereof.
 8. A fuel additive according to claim 7, wherein the alkyleneoxide is elected from the group consisting of ethylene oxide, propyleneoxide, or a mixture thereof.
 9. A fuel additive according to claim 1,wherein the alkylene-oxide-adducted hydrocarbyl amide is derived from analkylene-oxide-adduction reaction involving a coconut oil fatty acidamide with ethylene oxide and propylene oxide.
 10. A fuel compositionfor automotive fuels comprising a major amount of hydrocarbon boiling inthe gasoline or diesel range and, from 10 to 10,000 ppm weight perweight of fuel, of an alkylene-oxide-adducted hydrocarbyl amide havingfrom 3 to 50 moles of alkylene oxide per mole of hydrocarbyl amide. 11.The fuel composition according to claim 10, wherein thealkylene-oxide-adducted hydrocarbyl amide has from 3 to 20 moles ofalkylene oxide per mole of hydrocarbyl amide.
 12. The fuel compositionaccording to claim 11, wherein the alkylene-oxide-adducted hydrocarbylamide has from 4 to 15 moles of alkylene oxide per mole of hydrocarbylamide.
 13. A fuel composition according to claim 10, wherein thealkylene-oxide-adducted hydrocarbyl amide is derived from an alkyl oralkenyl amide having from 4 to 75 carbon atoms.
 14. A fuel compositionaccording to claim 13, wherein the alkylene-oxide-adducted hydrocarbylamide is derived from an alkyl or alkenyl amide having from 8 to 22carbon atoms.
 15. A fuel composition according to claim 14, wherein thealkyl or alkenyl amide is a coconut oil fatty acid amide.
 16. The fuelcomposition according to claim 10, wherein the alkylene oxide isselected from the group consisting of ethylene oxide, propylene oxide,butylene oxide, pentylene oxide, or mixtures thereof.
 17. A fuelcomposition according to claim 16, wherein the alkylene oxide is electedfrom the group consisting of ethylene oxide, propylene oxide, or amixture thereof.
 18. A fuel composition according to claim 10, whereinthe alkylene-oxide-adducted hydrocarbyl amide is derived from analkylene-oxide-adduction reaction involving a coconut oil fatty acidamide with ethylene oxide and propylene oxide.
 19. The fuel compositionaccording to claim 10, wherein the alkylene-oxide-adducted hydrocarbylamide is in the range of from 10 to 5,000 ppm weight per weight of fuel.20. The fuel composition according to claim 19, wherein thealkylene-oxide-adducted hydrocarbyl amide is in the range of from 10 to1,000 ppm weight per weight of fuel.
 21. A method of operating gasolineautomobile engines comprising operating said engine with the fuelcomposition according to claim
 10. 22. The method of operating gasolineautomobile engines according to claim 21, wherein the amount of alkyleneoxide is from 3 to 20 moles per mole of hydrocarbyl amide and saidalkylene oxide is selected from the group consisting of ethylene oxide,propylene oxide, butylene oxide, pentylene oxide, or mixtures thereof.23. A method of improving the acceleration performance of gasolineautomobile engines comprising additizing the fuel additive of claim 1 toa gasoline and operating said engine with said gasoline.
 24. The methodof improving the acceleration performance of gasoline automobile enginesaccording to claim 23, wherein the amount of alkylene oxide is from 3 to20 moles per mole of hydrocarbyl amide and said alkylene oxide isselected from the group consisting of ethylene oxide, propylene oxide,butylene oxide, pentylene oxide, or mixtures thereof.